Famous Gamblers: Stories of High Rollers

Since the first modern casinos were invented in the 1600s, countless gamblers have found wealth and glory. However, only a few among them are still remembered today for being famous gamblers. Sometimes, the players have become mythologized for their skills, while others serve as cautionary tales for their more controversial exploits.

In this guide, we’ve looked at the most famous gamblers that have played over the last two hundred years. We’ve begun by looking at history’s most famous gamblers before looking at some gamblers that have made waves in recent years. In the final section, we’ve discussed some celebrities who are also known for being gamblers.

Famous Gamblers From History

While the first incarnations of modern casinos date back to 1683 in Venice, widespread gambling didn’t reach the mainstream until the 1800s. Many associate gambling with the Wild West due to its popularity among pioneers, and there are countless gambling legends that have arisen from these times. The gamblers we’ve covered include:

• Wild Bill Hickok
• Charles Deville Wells
• Nick “The Greek” Dandolos
• Richard Canfield
• John “Bet-a-Million” Gates

Wild Bill Hickok

The story of Wild Bill Hickok is known far and wide and has been brought to life in movies and television for decades. The legend goes that Wild Bill, a famous Wild West gunfighter and law figure, was playing a game of five-card stud poker at a saloon in Deadwood.

With his back facing the food, he was dealt a hand of two black aces and two black eights. The fifth card is up for debate, but many suggest that it was the Nine of Diamonds. At that time, Jack McCall, a man known to dislike Hickok, entered the saloon and shot Wild Bill in the head from behind.

Since then, the poker hand of two black aces and two black eights has been known as the “Dead Man’s Hand”. The story was widely spread throughout the Wild West and has been a staple of the American legend ever since.

Charles Deville Wells

Charles Deville Wells was a British gambler who earned his legend status at the famous Monte Carlo Casino in the late 1800s. Wells came to the casino with the intention to rig the roulette wheel in his favor. While we will never know what his system was, it proved an immediate success.

With an initial bankroll of 4,000 francs, Wells began a winning streak that lasted for days. The story quickly spread, and many flocked to watch him build up his winnings. The legend goes that he broke the bank several times, leading the casino’s management to grow concerned about their financial prospects.

However, Wells’ streak eventually came to an end, and he eventually lost a substantial amount of his winnings. Despite this, the story of the world famous gambler has remained legendary ever since, and he is often referred to as “The Man Who Broke the Bank at Monte Carlo.”

Nick “The Greek” Dandolos

Nick “The Greek” Dandolos is often considered to be one of the best gamblers of all time due to his infamous high-stakes gambling exploits in the early 1900s. He earned a strong reputation for his large wagers, charming persona, stylish betting, and unrivaled skill at poker. The most famous story about “The Greek” involves a poker marathon.

Dandolos was competing against another famous gambler Johnny Moss in a poker match that lasted for months. They played several different variants with the biggest similarity being that the stakes were always high. Both players faced wins and losses over the months until one final game was proposed.

Dandolos bet his entire bankroll against Moss’ chips, which intimidated him into folding. The story is often held up as an example of the unpredictability and the thrills of high-stakes poker, with Dandolos celebrated for his skill at reading his opponents.

Richard Canfield

Richard Canfield’s achievements are closely tied to the history of American gambling, with his most notable success being the introduction of solitaire to casinos. While his gambling exploits were storied, he is perhaps best known for opening the Canfield Casino in Saratoga Springs, New York.

The establishment was frequented by the upper classes and wealthy due to its luxurious atmosphere and high-stakes gaming tables. The casino would be a blueprint for later casinos to open in the USA, with poker, roulette, and faro being its most popular games. However, it was his adaption of solitaire for gambling environments that was the biggest success.

Canfield’s solitaire could be played by several people at once and utilized a large table with columns of cards. The game drew huge crowds until Canfield’s operations were shut down due to legal issues. Although his success was short-lived, his role as a gambling innovator left a huge impression on gamblers of the time.

John “Bet-a-Million” Gates

You don’t get a nickname like “Bet-a-Million” without making a few exorbitant bets. The story of John Warne Gates is an interesting one. Starting his career as a barbed wire salesman, Gates earned a fortune by supplying the cattle industry with this new technology.

As his status and wealth expanded, Gates became famous for making large bets on a range of things. His most famous bet was in 1901 when he wagered $70,000 that he could move a heavy train by pulling a rope at the Pan-American Exposition in New York. He then amazed the crowd by managing to pull it with the help of some pulleys.

He earned a payout on his stake, which equates to millions of dollars in today’s money. Other famous bets involved the outcomes of elections and horse races. Gates is one of the more flamboyant famous bettors in gambling history and a reminder of the extravagant pre-war times.

Famous Gamblers of Modern Times

After the establishment of Las Vegas as a global gambling capital, the casino industry would be changed forever. As millions flocked to the city, the popularity of games such as blackjack and poker grew, and with it, so did the reputations of famous gamblers. In this section, we’ve looked at some of the most famous gamblers of modern times.

Edward Thorp

One of the most popular and controversial figures to emerge from the gambling world is the mathematician and author Edward Thorp. His most well-known achievement was his seminal book “Beat the Dealer,” which detailed how players count cards to increase their chances of winning at blackjack.

While working as a mathematics professor at MIT, Thorp developed a system to track the ratio of high to low cards left in a blackjack deck. After he published his book outlining the system, the impact was immediate. Thousands bought the book and many casinos had to change their rules to combat the risk of card counting.

While Edward Thorp tested his strategy numerous times and guaranteed a profit, he is now more known for his work in finances than for his contributions to gambling. It is estimated that he is worth over $800 million, which proves that he was really on to something.

Archie “The Greek” Karas

If Archie “The Greek” Karas’ luck didn’t dry up, he could easily be considered the greatest gambler of all time for his legendary gambling run in the 1990s. The story goes that Karas arrived in Las Vegas with just $50 in his pocket. He started by playing poker and quickly found success.

From there, he graduated to high-stakes poker tables, where his luck and skill produced even more success. Over the next few years, Karas’ wealth and fortune grew, and it is estimated that at one point he was worth over $40 million. A highlight of the streak was a shocking win of poker star Stu Ungar worth millions.

Karas’ story is a cautionary tale, though, as he started to face a losing streak. He began to earn a reputation for chasing losses and reckless playing, and within months, he had lost most of his fortune. Some believe that Karas has bet more money in casinos than anyone else in history.

Erik Seidel

Erik Seidel is one of the most well-known poker players in the world, having won nine WSOP bracelets over his long and successful career. While he isn’t at the top of the all-time money list, his story is one of the most interesting. He was first introduced to the game in the late 1980s by a friend while working as a trader in New York.

Despite being a newcomer, Seidel made it to the final table of the 1988 World Series of Poker Main Event. He finished as a runner-up, but this achievement was not lost on poker fans. This run wasn’t a flash in the pan too Over the next two decades, Seifel won multiple WSOP poker titles.

His biggest achievement was when he won the Super High Roller event at the Aussie Millions Poker Championship, earning over $1 million in prizes. That year saw several other high-profile wins, bringing his annual earnings to over $6 million.

Phil Ivey

Phil Ivey is a professional poker player who has achieved many great successes over his long career, including earning ten WSOP bracelets. However, Ivey is perhaps most famous for garnering controversy over his edge-sorting activities, which saw him banned from several high-profile casinos.

The scandal involved Ivey’s and a partner’s identification of small defects in the patterns of playing cards used in baccarat games. They then used these to their advantage and racked up millions of dollars in wins. When he was discovered, the casinos took Ivey to court for cheating and he lost some major cases.

Despite this setback, Ivey is still widely respected in the poker community and has a strong reputation for strategy and his calm approach to the game. Ivey’s live tournament wins hover at around $40 million, with one of his largest wins coming in at $2 million for a high-stakes poker tournament.

Don Johnson

Don Johnson is another casino gambler who came to prominence with his sophisticated blackjack play and ability to negotiate favorable conditions with casinos. It all began in 2011 when the businessman began a playing spree at several different Atlantic City casinos. A blackjack player, he chose games that allowed late surrenders and doubling down.

He also negotiated discounts on his losses. With these advantages, Johnson used card counting techniques, mathematics, and strategy to reap huge rewards. At the peak of his months-long streak, it is estimated that he had won between $15 and $20 million. This brought him national attention.

Because Johnson had exploited the system, he was never considered to be a cheater. He managed to turn the table on casinos, which usually benefit from the house edge, and amass a fortune. While the Atlantic City casinos likely amended these loopholes, people like Johnson are an example of skillful and strategic play.

High-Roller Celebrities

There are several A-list celebrities who have earned a reputation for their gambling activity and skills. With large bankrolls and special access to VIP tables and events, these stars are regularly seen at some of the world’s most luxurious casinos. We have covered three celebrity gamblers below.

Ben Affleck

Ben Affleck is perhaps the most famous gambler on this list. The actor and filmmaker known for Batman, Daredevil, and Good Will Hunting has been known to show an affinity for blackjack. This was especially the case in the early 2000s when Affleck won around $800,000 playing blackjack at the Hard Rock Casino in Las Vegas.

Affleck’s ability was put down to advantage play strategies such as card counting. For this reason, Affleck was reportedly banned from playing blackjack at the Hard Rock Casino in 2014. Nevertheless, Ben Affleck’s gambling skills are another indication of the star’s impressive intellect and talent.

Matt Damon

The actor Matt Damon is well understood to have a strong proclivity toward poker. As a long-time friend of Ben Affleck, he often accompanied him to Vegas for gambling trips. In recent times, they have played in World Series of Poker Main Events, even partnering with the organization to raise money for charity.

This may not come as a surprise to those who have seen Rounders, a cult film about high-stakes poker starring Matt Damon that is credited with reigniting the popularity of poker in the early 2000s. Importantly, Matt Damon is a major proponent of responsible gambling and has been cautious to not develop unhealthy habits.

Tobey Maguire

Tobey Maguire, the actor most famous for playing Spiderman, has a storied past in high-stakes poker games. At the height of his fame, he was known to frequent underground high-stakes poker games with stars such as Leonardo DiCaprio in Hollywood. These were fictionalized in the recent movie Molly’s Game.

Because these games weren’t technically legal, much of the details about them are still obscure.  However, rumors have circulated ever since about Maguire’s poker prowess, and he was known to be among the most successful players. Not only that, but he was even instrumental in organizing the games and making significant amounts of cash from hosting alone.

Conclusion

As this guide has covered, history is full of interesting and colorful characters that have had immense successes and crushing lows when it comes to gambling. If there is a lesson to be learned from each story, it’s that strategic and calculated gameplay can pay dividends and never play at casinos or online gambling sites in an irresponsible manner.

Frequently Asked Questions

Are you looking for quick answers to your questions about famous gamblers from history, keep reading. Below, we’ve provided brief responses to common queries about this interesting topic.